Trifluoroacetic acid → (S)-3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoropyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

HRID 335844Notes

Reaction equation

HRID 335844 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:20]4([CH2:24][S:23][C:22]([NH:25]C(=O)OC(C)(C)C)=[N:21]4)[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:33]5[C:34]([F:39])=[N:35][CH:36]=[CH:37][CH:38]=5)[CH:18]=4)[O:13][C:10]3=[N:11][CH:12]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:8]=[C:9]3[C@:20]4([CH2:24][S:23][C:22]([NH2:25])=[N:21]4)[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:33]5[C:34]([F:39])=[N:35][CH:36]=[CH:37][CH:38]=5)[CH:18]=4)[O:13][C:10]3=[N:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67383473tert-butyl 3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoropyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazole]-2'-ylcarbamate

Product 1

HCID 53464448(S)-3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoropyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A RBF was charged with tert-butyl 3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazole]-2′-ylcarbamate (0.091 g, 0.166 mmol). The material was dissolved in 0.5 mL of CH2Cl2 and TFA (0.149 mL, 1.932 mmol) was added. The reaction was heated to 50° C. and stirred for one hour. The reaction was concentrated, diluted with CH2Cl2 and washed with saturated sodium bicarbonate solution. The aqueous layer was extracted with CH2Cl2, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated to afford (S)-3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine as an off-white solid. MS m/z=447.3 [M+H]+. Calculated for C24H19FN4O2S: 446.12.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with CH2Cl2
  3. washwashed with saturated sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ba1f939ac62b4621833667dafe988de4
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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